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SML0120

Sigma-Aldrich

Perhexiline maleate salt

≥98% (HPLC)

Synonym(s):

2-(2,2-Dicyclohexylethyl)piperidine

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About This Item

Empirical Formula (Hill Notation):
C19H35N · C4H4O4
CAS Number:
6724-53-4
Molecular Weight:
393.56
EC Number:
229-775-5
MDL number:
MFCD00057329
UNSPSC Code:
12352200
PubChem Substance ID:
329825171
NACRES:
NA.25

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥5 mg/mL

storage temp.

2-8°C

SMILES string

OC(=O)\C=C/C(O)=O.C1CCC(CC1)C(CC2CCCCN2)C3CCCCC3

InChI

1S/C19H35N.C4H4O4/c1-3-9-16(10-4-1)19(17-11-5-2-6-12-17)15-18-13-7-8-14-20-18;5-3(6)1-2-4(7)8/h16-20H,1-15H2;1-2H,(H,5,6)(H,7,8)/b;2-1-

InChI key

JDZOTSLZMQDFLG-BTJKTKAUSA-N

Gene Information

human ... CPT1B(1375) , CPT2(1376) , MTOR(2475)

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General description

Perhexiline maleate regulates coronary vasodilatation and blocks exercise-induced tachycardia. It is used to treat angina pectoris and variant angina. Perhexiline maleate functions as a cardiac metabolic agent. It is associated with peripheral neuropathy, high intracranial pressure with papilledema and proximal myopathy.

Application

Perhexiline maleate salt has been used as a stock for worm lifespan assay. It has also been used to block fatty acid oxidation.
Perhexiline maleate salt has been used to block fatty acid oxidation. It has also been used as 5′ adenosine monophosphate-activated protein kinase (AMPK) activator and in worm lifespan assay.

Biochem/physiol Actions

Perhexiline maleate is an anti-anginal metabolic modulator. It inhibits the mitochondrial enzyme carnitine palmitoyltransferase CPT-1 and to a lesser extent CPT-2. This causes a shift in myocardial substrate utilisation from long chain fatty acids to carbohydrates, resulting in increased glucose and lactate utilization and increased ATP production for the same O2 consumption as before and consequently increases myocardial efficiency. Perhexiline maleate was also recently found to inhibit the activity of mTORC1.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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B D Walker et al.
British journal of pharmacology, 127(1), 243-251 (1999-06-16)
Perhexiline has been used as an anti-anginal agent for over 25 years, and is known to cause QT prolongation and torsades de pointes. We hypothesized that the cellular basis for these effects was blockade of I(Kr). A stable transfection of
M A Mariscal et al.
Biochemical pharmacology, 37(18), 3461-3465 (1988-09-15)
The effect of the antianginal agent perhexiline maleate (160 mg/kg i.g., daily for 4 days) on the biliary excretion of sulfobromophthalein (BSP) and BSP-glutathione and the hepatic activity of glutathione S-transferases was investigated in Wistar rats. Perhexiline maleate caused a
B J Foster et al.
Cancer chemotherapy and pharmacology, 22(2), 147-152 (1988-01-01)
The clinical utility of adriamycin in the treatment of patients with metastatic breast cancer is often-limited by the development of drug resistance. It has been recognized that in addition to the development of primary resistance against adriamycin, malignant cells can
Raised intracranial pressure due to perhexiline maleate
Stephens WP, et al.
British Medical Journal, 1(6104), 21-21 (1978)
V Shacoori et al.
Research communications in chemical pathology and pharmacology, 59(2), 161-172 (1988-02-01)
Human clinical observations and in vivo studies have shown that the amphiphilic drug perhexiline maleate is responsible for lipidosis storage disorders. When the drug was incubated in vivo with rat brain homogenates, the ouabain-sensitive (Na+,K+)-ATPase and the Mg++-ATPase activities were
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